Self-assembled tetrazine cryptophane for ion pair recognition and guest release by cage disassembly

Hereby, we describe the synthesis of a self-assembled syn-cryptophane using dynamic nucleophilic aromatic substitution of tetrazines. 1H NMR cage titrations reveal that the tetramethylammonium cation binds under slow exchange conditions while counter-anions show a fast exchange regime. Finally, the cryptophane can be disassembled by the addition of thiols allowing guest release. A cryptophane is able to release guests by the addition of thiols thanks to the dynamic nucleophilic substitution of tetrazines.